Irregular warfare (IW), deeply interwoven with cultural, political, and sociological factors, has historically relied on the agility and adaptability of intelligence operations. As the fabric of warfare has evolved from the dense jungles of Vietnam to the digital frontlines of Ukraine, so too has the nature of intelligence shifted, from human-centric insights to technology-driven reconnaissance. Moving forward, the fusion of advanced technological innovations with intrinsic human understanding will redefine the essence of intelligence in IW, making it a more potent force in navigating the complexities of future unconventional conflicts. By delving into the distinct epochs of Vietnam, Afghanistan, and Ukraine, we can discern the shifting sands of intelligence in support of IW and envision what the future might hold. Many will claim that the future of intelligence lies in technology and this claim has taken the front stage in the past, but it was unequivocally refuted with many mishaps that could have been prevented. Let’s look at the evolution of intelligence and see what the future ahead looks like for it.